A facile method for the solution and solid-phase synthesis of substituted [3.3.1] bicycles

Organic Letters

Volumn 1, Issue 5, 1999, Pages 807-810

  Nicolaou, K C ^a   Pfefferkorn, Jeffrey A ^a   Cao, Guo Qiang ^a   Kim, Sanghee ^a   Kessabi, Jilali ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001027385     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990791d     Document Type: Article

References (35)

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7. For examples, see: Gustafson, K. R.; Blunt, J. W.; Munro, M. H. G.; Fuller, R. W.; McKee, T. C.; Cardelina, J. H.; McMahon, J.; Gragg, G. M.; Boyd, M. R. Tetrahedron 1992, 48, 10093-10102. Iinuma, M.; Tosa, H.; Tanaka, T.; Kanamaru, S.; Asai, F.; Kobayashi, Y.; Miyauchi, K.; Shimano, R. Biol. Pharm. Bull. 1996, 18, 311-314. Alves, T. M. A.; Alves, R. O.; Romanha, A. J.; Santos, M. H.; Nagem, T. J.; Zani, C. L. J. Nat. Prod. 1999, 62, 369-371. Oliveira, C. M. A.; Porto, A. M.; Bittrich, V.; Vencato, I.; Marsaioli, A. J. Tetrahedron Lett. 1996, 37, 6427-6430.
8. For examples, see: Gustafson, K. R.; Blunt, J. W.; Munro, M. H. G.; Fuller, R. W.; McKee, T. C.; Cardelina, J. H.; McMahon, J.; Gragg, G. M.; Boyd, M. R. Tetrahedron 1992, 48, 10093-10102. Iinuma, M.; Tosa, H.; Tanaka, T.; Kanamaru, S.; Asai, F.; Kobayashi, Y.; Miyauchi, K.; Shimano, R. Biol. Pharm. Bull. 1996, 18, 311-314. Alves, T. M. A.; Alves, R. O.; Romanha, A. J.; Santos, M. H.; Nagem, T. J.; Zani, C. L. J. Nat. Prod. 1999, 62, 369-371. Oliveira, C. M. A.; Porto, A. M.; Bittrich, V.; Vencato, I.; Marsaioli, A. J. Tetrahedron Lett. 1996, 37, 6427-6430.
9. Oliveira, C. M. A.; Porto, A. L. M.; Bittrich, V.; Marsaioli, A. J. Phytochemistry 1999, 50, 1073-1079.
10. For examples, see: Taeschler, C.; Sorenson, T. S. J. Org. Chem. 1998, 63, 5704-5705. Harding, K. E.; Clement, B. A.; Moreno, L.; Katalinic, J. P. J. Org. Chem. 1981, 46, 940-948. Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. Peters, J. A. Synthesis 1979, 321-336. Lu, X.; Huang, Y. Tetrahedron Lett. 1986, 27, 1615-1616.
11. For examples, see: Taeschler, C.; Sorenson, T. S. J. Org. Chem. 1998, 63, 5704-5705. Harding, K. E.; Clement, B. A.; Moreno, L.; Katalinic, J. P. J. Org. Chem. 1981, 46, 940-948. Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. Peters, J. A. Synthesis 1979, 321-336. Lu, X.; Huang, Y. Tetrahedron Lett. 1986, 27, 1615-1616.
12. For examples, see: Taeschler, C.; Sorenson, T. S. J. Org. Chem. 1998, 63, 5704-5705. Harding, K. E.; Clement, B. A.; Moreno, L.; Katalinic, J. P. J. Org. Chem. 1981, 46, 940-948. Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. Peters, J. A. Synthesis 1979, 321-336. Lu, X.; Huang, Y. Tetrahedron Lett. 1986, 27, 1615-1616.
13. For examples, see: Taeschler, C.; Sorenson, T. S. J. Org. Chem. 1998, 63, 5704-5705. Harding, K. E.; Clement, B. A.; Moreno, L.; Katalinic, J. P. J. Org. Chem. 1981, 46, 940-948. Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. Peters, J. A. Synthesis 1979, 321-336. Lu, X.; Huang, Y. Tetrahedron Lett. 1986, 27, 1615-1616.
14. For examples, see: Taeschler, C.; Sorenson, T. S. J. Org. Chem. 1998, 63, 5704-5705. Harding, K. E.; Clement, B. A.; Moreno, L.; Katalinic, J. P. J. Org. Chem. 1981, 46, 940-948. Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. Peters, J. A. Synthesis 1979, 321-336. Lu, X.; Huang, Y. Tetrahedron Lett. 1986, 27, 1615-1616.
15. To the best of our knowledge, no substituted 2,2-dimethylbicyclo-[3.3.1]nonan-9-one wherein both bridgehead positions are quaternary has been reported. For examples of the construction of substituted 2,2-dimethylbicyclo[3.3.1]nonan-9-one with at least one quaternary bridgehead position, see: Firrel, N. F.; Hickmott, P. W.; Hopkins, B. J. J. Chem Soc. C 1970, 1477-1480. Dauben, W. G.; Bunce, R. A. J. Org. Chem. 1983, 48, 4642-4648. Gambacorta, A.; Fabrizi, G.; Bovicelli, P. Tetrahedron 1992, 48, 4459-4464. Evans, E. H.; Hewson, A. T.; March, L. A.; Nowell, I. W.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. 1 1987, 137-149.
16. To the best of our knowledge, no substituted 2,2-dimethylbicyclo- [3.3.1]nonan-9-one wherein both bridgehead positions are quaternary has been reported. For examples of the construction of substituted 2,2- dimethylbicyclo[3.3.1]nonan-9-one with at least one quaternary bridgehead position, see: Firrel, N. F.; Hickmott, P. W.; Hopkins, B. J. J. Chem Soc. C 1970, 1477-1480. Dauben, W. G.; Bunce, R. A. J. Org. Chem. 1983, 48, 4642-4648. Gambacorta, A.; Fabrizi, G.; Bovicelli, P. Tetrahedron 1992, 48, 4459-4464. Evans, E. H.; Hewson, A. T.; March, L. A.; Nowell, I. W.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. 1 1987, 137-149.
17. To the best of our knowledge, no substituted 2,2-dimethylbicyclo- [3.3.1]nonan-9-one wherein both bridgehead positions are quaternary has been reported. For examples of the construction of substituted 2,2- dimethylbicyclo[3.3.1]nonan-9-one with at least one quaternary bridgehead position, see: Firrel, N. F.; Hickmott, P. W.; Hopkins, B. J. J. Chem Soc. C 1970, 1477-1480. Dauben, W. G.; Bunce, R. A. J. Org. Chem. 1983, 48, 4642-4648. Gambacorta, A.; Fabrizi, G.; Bovicelli, P. Tetrahedron 1992, 48, 4459-4464. Evans, E. H.; Hewson, A. T.; March, L. A.; Nowell, I. W.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. 1 1987, 137-149.
18. To the best of our knowledge, no substituted 2,2-dimethylbicyclo- [3.3.1]nonan-9-one wherein both bridgehead positions are quaternary has been reported. For examples of the construction of substituted 2,2- dimethylbicyclo[3.3.1]nonan-9-one with at least one quaternary bridgehead position, see: Firrel, N. F.; Hickmott, P. W.; Hopkins, B. J. J. Chem Soc. C 1970, 1477-1480. Dauben, W. G.; Bunce, R. A. J. Org. Chem. 1983, 48, 4642-4648. Gambacorta, A.; Fabrizi, G.; Bovicelli, P. Tetrahedron 1992, 48, 4459-4464. Evans, E. H.; Hewson, A. T.; March, L. A.; Nowell, I. W.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. 1 1987, 137-149.
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29. Review: Kozikowski, A. P.; Tuckmantel, W. Acc. Chem. Res. 1999, 32, to appear in the August issue on p 641 and available via ACS Articles ASAP until print publication.
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33. Molecular modeling studies are in progress.
34. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401. For a similar example, see: Ley, S. V.; Mynett, D. M.; Root, W. J. Synlett 1995, 1017-1020.
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